Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality† †This article is part of a ChemComm ‘Catalysis in Organic Synthesis’ web-theme issue showcasing high quality research in organic chemistry. Please see our website (http://www.rsc.org/chemcomm/organicwebtheme2009) to access the other papers in this issue. ‡ ‡Electronic supplementary information (ESI) available: Procedures for the asymmetric autocatalysis in the presence of 1 and 2, the preparation of enantiomers of 1 and 2, and the determination of the enantiomeric purity of 1 and 2. See DOI: 10.1039/b908754k Click here for additional data file.

摘要

Achiral meteoritic glycine and α-methylalanine, with hydrogen isotope (D/H) chirality, acted as the source of chirality in asymmetric autocatalysis with amplification of ee to afford highly enantioenriched 5-pyrimidyl alkanols.